Hydrochloric Acid → HCID 73441852, compound

HRID 530686Notes

Reaction equation

HRID 530686 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[C:10](=[O:30])[NH:11][C:12]1[S:13][C:14]([CH3:29])=[C:15]([CH:26]2[CH2:28][CH2:27]2)[C:16]=1[C:17]1[O:21][N:20]=[C:19]([C:22]([F:25])([F:24])[F:23])[N:18]=1)=[O:4].O.Cl.CCOC(C)=O>O1CCOCC1>[CH:26]1([C:15]2[C:16]([C:17]3[O:21][N:20]=[C:19]([C:22]([F:23])([F:24])[F:25])[N:18]=3)=[C:12]([NH:11][C:10]([C:6]3[CH2:7][CH2:8][CH2:9][C:5]=3[C:3]([OH:4])=[O:2])=[O:30])[S:13][C:14]=2[CH3:29])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 90047395HCID 90047395, compound2×

Product 1

HCID 73441852HCID 73441852, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[4-cyclopropyl-5-methyl-3-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-thiophen-2-ylcarbamoyl]-cyclopent-1-enecarboxylic acid methyl ester (80 mg, 181 μmol, intermediate 7) in dioxane (3 mL) was added H2O (3 mL) and LiOH monohydrate (9.51 mg, 227 μmol) and the resulting clear solution was stirred at RT for 8 h. The reaction mixture was poured on 100 mL 1M aqueous HCl and 100 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 100 mL EtOAc. The organic layers were washed with 100 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (Flashmaster) system eluting with a gradient of CH2Cl2:MeOH (100:0 to 80:20). Yellow solid (57 mg, 74%). MS (ESI): m/z=428.088 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 100 mL EtOAc
  3. washThe organic layers were washed with 100 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of CH2Cl2:MeOH (100:0 to 80:20)

Sources & evidence

ORD record
ord-eca30ccaac474290b4cbb0ec47a06a82
Source dataset
uspto-grants-2016_05
Patent number
US09353102B2

Reaction notes

Loading…